US5883167A - Process for the preparation of highly coloured diazo pigment mixtures - Google Patents

Process for the preparation of highly coloured diazo pigment mixtures Download PDF

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Publication number
US5883167A
US5883167A US08/903,467 US90346797A US5883167A US 5883167 A US5883167 A US 5883167A US 90346797 A US90346797 A US 90346797A US 5883167 A US5883167 A US 5883167A
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Prior art keywords
mixture
mol
molar ratio
iii
molecular weight
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US08/903,467
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English (en)
Inventor
Bernhard Medinger
Daniel Andrey
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BASF Corp
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Ciba Specialty Chemicals Corp
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Assigned to CIBA SPECIALTY CHEMICALS CORP. reassignment CIBA SPECIALTY CHEMICALS CORP. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ANDREY, DANIEL, MEDINGER, BERNHARD
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/23—Azo-compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/32—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines
    • C09B43/38—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines by reacting two or more ortho-hydroxy naphthoic acid dyes with polyamines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0055—Mixtures of two or more disazo dyes

Definitions

  • the present invention relates to a process for the preparation of highly coloured diazo pigment mixtures by condensing 2 mol of an azocarboxylic acid chloride with 1 mol of a mixture consisting of 2 or 3 different phenylene diamines.
  • the products obtained are distinguished by outstanding colour strength and/or chroma.
  • GB 1 595 489 discloses that diazo pigment mixtures having good colouristic properties are obtained by condensing 2 mol of a mixture of different azocarboxylic acid chlorides of the general formula ##STR3## with 1 mol of a diamine of formula ##STR4##
  • Page 8, lines 8 and 9 states that it is also possible to use mixtures of different diamines instead of uniform diamines without any surprising effect being thereby attained.
  • this invention relates to a process for the preparation of diazo pigment mixtures, which comprises condensing 2 mol of an azocarboxylic acid chloride of formula ##STR7## with 1 mol of a mixture of diamines of formulae ##STR8## at a molar ratio of II:III:IV from 0-30:5-60:40-95,
  • the azocarboxylic acid chloride of formula I and the diamines of formulae II, III and IV are known substances (e.g. from GB 1 595 489).
  • condensation is carried out by customary methods such as those described, inter alia, in GB 1 595 489.
  • a solid solution is characterised by its X-ray diffraction patterns, the X-ray diffraction patterns of the solid solution being different from those of the single components and of the physical mixture of the single components.
  • the mixed condensates obtained by the process of this invention are valuable pigments for colouring high molecular weight organic material.
  • High molecular weight organic materials which can be coloured or pigmented with the pigments obtained according to this invention are typically cellulose ethers and esters, such as ethyl cellulose, nitrocellulose, cellulose acetate, cellulose butyrate, natural or synthetic resins, such as polymerisation or condensation resins, e.g.
  • aminoplasts in particular urea/ formaldehyde resins and melamine/formaldehyde resins, alkyd resins, phenolic plastics, polycarbonates, polyolefins, polystyrene, polyvinyl chloride, polyamides, polyurethanes, polyesters, ABS, polyphenylene oxides, rubber, casein, silicone and silicone resins, singly or in admixture.
  • the indicated high molecular weight organic compounds can be obtained singly or as mixtures in the form of plastics, melts or in the form of spinning solutions, varnishes, paints or printing inks. Depending on the end use requirement, it is expedient to use the novel pigments as toners or in the form or preparations.
  • the pigments prepared according to this invention can be used in an amount of 0.01 to 30% by weight, preferably of 0.1 to 10% by weight, based on the high molecular weight organic material to be pigmented.
  • the pigmenting of the high molecular weight organic substances with the pigments prepared according to this invention is conveniently effected by incorporating such pigments by themselves or in the form of masterbatches in these substrates using roll mills, mixing or milling apparatus.
  • the pigmented material is then brought into the desired final form by methods which are known per se, conveniently by calendering, moulding, extruding, coating, casting or by injection moulding.
  • plasticisers are typically esters of phosphoric acid, phthalic acid or sebacic acid.
  • the plasticisers may be incorporated into the pigments prepared according to this invention before or after working the pigments into the polymers. To obtain different shades, it is also possible to add to the high molecular weight organic materials fillers or other chromophoric components such as white, coloured or black pigments in any amount, in addition to the pigments prepared according to this invention.
  • the high molecular weight organic materials and the pigments prepared according to this invention together with optional additives such as fillers, other pigments, siccatives or plasticisers, are finely dispersed or dissolved in a common organic solvent or solvent mixture.
  • the procedure may be such that the individual components by themselves, or also several jointly, are dispersed or dissolved in the solvent and thereafter all the components are mixed.
  • the pigments prepared according to this invention are particularly suitable for colouring plastic materials, preferably polyolefins and, in particular, polypropylene fibres.
  • the pigments prepared according to this invention are distinguished by good allround pigment properties, such as good dispersibility, good fastness to migration, heat, light and weathering as well as good opacity and, in particular, very high colour strength and purity.
  • the precipitated crystalline azo dye carboxylic acid chloride is isolated by filtration, wash ed with a small amount of cold o-dichlorobenzene and then with petroleum ether, and is then dried in a vacuum drying oven at 70° C.
  • This pigment suspension is cooled, with stirring, to room temperature and then charged with 200 g of methanol, heated to 60° C. The mixture is heated to 60° C. and then filtered at this temperature. The residue is washed with warm methanol and then with water. After drying in the vacuum drying oven at 60° C., 8.1 g of a diazo pigment mixture are obtained, consisting of 10 mol % of C.I. Pigment Red 166, 10 mol % of C.I. Pigment Red 144 and 80 mol % of C.I. Pigment Red 214 which, compared to the single components as well as to a corresponding physical mixture, has a surprisingly higher colour strength and chroma.
  • Example 1b The general procedure of Example 1b) is repeated, with the sole exception that the diamine mixture consisting of 0.11 g of p-phenylenediamine, 0.11 g of 2-chloro-p-phenylenediamine and 1.42 g of 1,4-diamino-2,5-dichlorobenzene is replaced with a diamine mixture consisting of 0.14 g of 2-chloro-p-phenylenediamine and 1.59 g of 1,4-diamino-2,5-dichlorobenzene. 6.8 g of a diazo pigment mixture are obtained, consisting of 10mol mol % of C.I. Pigment Red 144 and 90 mol % of C.I. Pigment Red 214 which, compared to the single components as well as to a corresponding physical mixture, has a surprisingly higher colour strength and chroma.
  • a diazo pigment mixture consisting of 10mol mol % of C.I. Pigment Red 144 and 90 mol %
  • Example 1b The general procedure of Example 1b) is repeated, with the sole exception that the diamine mixture consisting of 0.11 g of p-phenylenediamine, 0.11 g of 2-chloro-p-phenylenediamine and 1.42 g of 1,4-diamino-2,5-dichlorobenzene is replaced with a diamine mixture consisting of 0.36 g of 2-chloro-p-phenylenediamine and 1.32 g of 1,4-diamino-2,5-dichlorobenzene. 7.6 g of a diazo pigment mixture are obtained, consisting of 25 mol % of C.I. Pigment Red 144 and 75 mol % of C.I. Pigment Red 214 which, compared to the single components as well as to a corresponding physical mixture, has a surprisingly higher colour strength and chroma.
  • a diazo pigment mixture consisting of 25 mol % of C.I. Pigment Red 144 and 75 mol % of C
  • Example 1b The general procedure of Example 1b) is repeated, with the sole exception that the diamine mixture consisting of 0.11 g of p-phenylenediamine, 0.11 g of 2-chloro-p-phenylenediamine and 1.42 g of 1,4-diamino-2,5-dichlorobenzene is replaced with a diamine mixture consisting of 0.27 g of p-phenylenediamine, 0.36 g of 2-chloro-p-phenylenediamine and 0.89 g of 1,4-diamino-2,5-dichlorobenzene. 7.8 g of a diazo pigment mixture are obtained, consisting of 25 mol % of C.I.
  • Pigment Red 166 25 mol % of C.I. Pigment Red 144 and 50 mol % of C.I. Pigment Red 214 which, compared to the single components as well as to a corresponding physical mixture, has a surprisingly higher colour strength and chroma.
  • This product is a solid solution, the X-ray diffraction spectrum of which differs from that of the single components and of the corresponding physical mixture of the single components.
  • Example 1b The general procedure of Example 1b) is repeated, with the sole exception that the diamine mixture consisting of 0.11 g of p-phenylenediamine, 0.11 g of 2-chloro-p-phenylenediamine and 1.42 g of 1,4-diamino-2,5-dichlorobenzene is replaced with a diamine mixture consisting of 0.72 g of 2-chloro-p-phenylenediamine and 0.89 g of 1,4-diamino-2,5-dichlorobenzene.
  • 8.1 g of a diazo pigment mixture are obtained, consisting of 50 mol % of C.I. Pigment Red 144 and 50 mol % of C.I. Pigment Red 214 which, compared to the single components as well as to a corresponding physical mixture, has a surprisingly higher colour strength and chroma.
  • a diazo pigment mixture in accordance with Example 1 0.04 g of a diazo pigment mixture in accordance with Example 1 are mixed with 13.3 g of polyvinyl chloride (PVC EVIPOL®SH 7020, EVC GmbH, Frankfurt a.M.), 1 g of TiO 2 and 7.3 ml of a base mixture consisting of
  • the mixture is processed to a thin highly coloured red foil on a roll mill over 8 minutes at a roll mill temperature of 165° C.
  • Example 4 400 g of polypropylene granulate (DAPLEN® PT-55, Chemie LINZ) and 4 g of the pigment obtained in accordance with Example 4 are intimately mixed in a mixer drum.
  • the granulate treated in this manner is spun at 260°-285° C. by the melt spinning process, giving red fibres having excellent textile properties, such as fastness to light and wet treatment, as well as excellent colour strength and chroma.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Artificial Filaments (AREA)
  • Coloring (AREA)
  • Paints Or Removers (AREA)
  • Paper (AREA)
US08/903,467 1996-07-31 1997-07-31 Process for the preparation of highly coloured diazo pigment mixtures Expired - Lifetime US5883167A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US08/903,467 US5883167A (en) 1996-07-31 1997-07-31 Process for the preparation of highly coloured diazo pigment mixtures

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH190796 1996-07-31
US08/903,467 US5883167A (en) 1996-07-31 1997-07-31 Process for the preparation of highly coloured diazo pigment mixtures

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US (1) US5883167A (enExample)
EP (1) EP0822235B1 (enExample)
JP (1) JP3999312B2 (enExample)
KR (1) KR100469183B1 (enExample)
CN (1) CN1076370C (enExample)
CZ (1) CZ242297A3 (enExample)
DE (1) DE59706222D1 (enExample)
TW (1) TW411359B (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070125263A1 (en) * 2003-11-14 2007-06-07 Joachim Weber Pigment compositions consisting of a yellow disazo pigment and an organic pigment
US20090101874A1 (en) * 2003-11-14 2009-04-23 Joachim Weber Pigment compositions consisting of an organic yellow pigment and a phthalocyanine pigment
US20090105425A1 (en) * 2005-04-06 2009-04-23 Michael Roth Azo Compounds for Polypropylene Degradation

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI392708B (zh) * 2005-04-19 2013-04-11 Dainichiseika Color Chem 顏料分散劑及其使用
CN102816457B (zh) * 2012-08-23 2013-12-11 鞍山七彩化学股份有限公司 一种高着色强度的红色偶氮缩合混合颜料及其制备方法
DE102015121562B4 (de) 2015-12-10 2021-05-06 Coroplast Fritz Müller Gmbh & Co. Kg Hochtemperaturbeständiges farbiges, insbesondere orangefarbiges, Klebeband, Verfahren zu seiner Herstellung, Verwendung eines Trägers zu seiner Herstellung sowie Verwendung des Klebebandes zur Herstellung von Kabelbäumen
CN115772336B (zh) * 2022-11-15 2024-02-20 双乐颜料泰兴市有限公司 一种紫色有机颜料的制备

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1595489A (en) * 1976-12-31 1981-08-12 Ciba Geigy Ag Process for the production of azo pigments
US5518539A (en) * 1993-11-22 1996-05-21 Ciba-Geigy Corporation Process for the preparation of synergistic pigment mixtures

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5243848A (en) * 1975-10-06 1977-04-06 Nippon Kayaku Co Ltd Method for coloring high polymeric organic materials

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1595489A (en) * 1976-12-31 1981-08-12 Ciba Geigy Ag Process for the production of azo pigments
US5518539A (en) * 1993-11-22 1996-05-21 Ciba-Geigy Corporation Process for the preparation of synergistic pigment mixtures

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Chem. Abstr. vol. 83, No. 2, 12161e, (1975). *
Derwent Abstract 77 35332Y (JP 52043848). *
Derwent Abstract 77-35332Y (JP 52043848).

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070125263A1 (en) * 2003-11-14 2007-06-07 Joachim Weber Pigment compositions consisting of a yellow disazo pigment and an organic pigment
US7311769B2 (en) * 2003-11-14 2007-12-25 Clariant Produkte (Deutschland) Gmbh Pigment compositions consisting of a yellow disazo pigment and an organic pigment
US20090101874A1 (en) * 2003-11-14 2009-04-23 Joachim Weber Pigment compositions consisting of an organic yellow pigment and a phthalocyanine pigment
US20090105425A1 (en) * 2005-04-06 2009-04-23 Michael Roth Azo Compounds for Polypropylene Degradation
US8461272B2 (en) 2005-04-06 2013-06-11 Basf Se Azo compounds for polypropylene degradation

Also Published As

Publication number Publication date
EP0822235B1 (de) 2002-01-30
KR100469183B1 (ko) 2005-06-16
DE59706222D1 (de) 2002-03-14
JP3999312B2 (ja) 2007-10-31
CZ242297A3 (cs) 1998-06-17
EP0822235A2 (de) 1998-02-04
TW411359B (en) 2000-11-11
CN1076370C (zh) 2001-12-19
JPH1081831A (ja) 1998-03-31
KR980009394A (ko) 1998-04-30
CN1173520A (zh) 1998-02-18
EP0822235A3 (de) 1998-08-26

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